2-hydroxy-4-oxo-1H-quinoline-3-carbonitrile

Base Information

• Chemical Name: 2-hydroxy-4-oxo-1H-quinoline-3-carbonitrile
• CAS No.: 15000-43-8
• Molecular Formula: C₁₀H₆N₂O₂
• Molecular Weight: 186.17
• Hs Code.: 2933499090
• Mol file: 15000-43-8.mol

Synonyms:3-Quinolinecarbonitrile,2,4-dihydroxy- (8CI); 3-Cyano-4-hydroxycarbostyril; NSC 691971

Chemical Property of 2-hydroxy-4-oxo-1H-quinoline-3-carbonitrile

Chemical Property:

• Vapor Pressure: 0.000378mmHg at 25°C
• Melting Point: 292-295 °C (decomp)
• Boiling Point: 304.6°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 138°C
• PSA: 76.88000
• Density: 1.47g/cm³
• LogP: 1.10538

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-hydroxy-4-oxo-1H-quinoline-3-carbonitrile

There total 20 articles about 2-hydroxy-4-oxo-1H-quinoline-3-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

methyl [(2-ethoxycarbonylaminophenyl)hydroxymethylidene]cyanoacetate → 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (15000-43-8)

Guidance literature:

With methanol; sodium; for 5h; Heating;

DOI:10.3987/com-99-8508

Reference yield: 92.0%

methyl 2-(2-cyanoacetamido)benzoate (154325-57-2) → 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (15000-43-8)

Guidance literature:

With methanol; sodium methylate; for 10h; Ambient temperature;

DOI:10.1007/BF00534390

Reference yield: 91.0%

3-(2-Acetylamino-phenyl)-2-cyano-3-oxo-propionic acid ethyl ester (1026672-88-7) → 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (15000-43-8)

Guidance literature:

With sodium ethanolate; In ethanol; 1.) reflux, 5 h, 2.) r.t., overnight;

DOI:10.1039/p19960002909

upstream raw materials:

ethyl N-<2-(2-cyanoacetyl)phenyl>carbamate

ethyl N-<2-(bromoacetyl)phenyl>carbamate

isatoic anhydride

ethyl 2-cyanoacetate

Downstream raw materials:

2,4-Dichloroquinoline-3-carbonitrile

4-chloro-2-oxo-1,2-dihvdroquinoline-3-carbonitrile

4-phenyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile

2-nitro-quinoline

Refernces

• 1、 Alghanmi, Reem M.,Mekheimer, Ramadan A.,Habeeb, Moustafa M.. "Spectroscopic studies on the proton transfer reactions of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-carbonitrile with different amines in acetonitrile". . p. 78 - 85. Retrieved 2012.
• 2、 Abdulla,Unger. "N aryl 3 cyanoazetidin 2,4 diones. A correction". . p. 1781 - 1784. Retrieved 1974.
• 3、 -. "AZA-CYANOQUINOLINONE PDE9 INHIBITORS". Page/Page column 26. . Retrieved 2017/02/24.